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Worst UFA contracts

The past week has been a furious one for NHL unrestricted free agent signings. Some were astute at a time when GMs are pressured to be anything but.

In Vancouver, Mike Gillis stared down the Sedins’ demands for 12-year contracts and locked the twins up for five. In Anaheim, Scott Niedermayer now has the 12th-highest salary in the league among defensemen, despite his top-five game. And in Colorado, neophyte GM Greg Sherman upgraded his goaltending with Craig Anderson for less than $2 million per season.

But, of course, there have been more than a few gun-jumpers and panicky spenders this past week – it wouldn’t be NHL free agent frenzy otherwise. The usual suspects are involved, but Glen Sather isn’t alone. It’s tough to tell what makes a bad deal in the NHL these days, but in the spirit of calling a spade (or 10) a spade, this week the THN Top 10 explores the worst 2009 UFA signings.

10. Chris Neil, RW, Ottawa – four years, $8 million
The 30-year-old enforcer plays a role and plays it well, but that role isn’t worth two large per season. Neil has 30 points in his past 128 NHL games and has never had more than 33 in a season. Over the past two years, he has essentially gone from an energy player with some pop in his blade and his fists to a pugilist, who are a dime a dozen in the NHL.

9. Mike Komisarek, D, Toronto – five years, $22.5 million
The former Canadien, 27, is a punishing bodychecker with a defense-first attitude who was looking to be developing into a premier shutdown guy. But he regressed last season, looked intimidated at times and became a whipping boy in Montreal. He’s the prototypical Brian Burke blueliner, but is no Robyn Regehr, who Komisarek now makes more money than.

8. Colton Orr, RW, Toronto – four years, $4 million
A million dollars is really just pocket change in today’s NHL. But Orr’s highest single-season point total of his past 11 seasons is 13, which he managed in the Western League in 2000-01 with Swift Current and Kamloops. Orr, 27, is nothing more than a goon, tougher than most, but less skilled than, say, Neil. And now, like Neil, he’s overpaid.

7. Nik Antropov, RW, Atlanta – four years, $16 million
Versatile, but maddening, Antropov teased Maple Leafs fans for nearly a decade with his size and ability to stickhandle in a phone booth. His ability to stay healthy, however, was another story. Entering his 10th NHL season, the big Kazakh has just once managed to stay in the lineup for a full season – last season – and has topped 20 goals and 50 points only twice. His lack of foot speed means he will have trouble keeping up with Ilya Kovalchuk, whom Antropov, 29, was presumably signed to play with.

6. Marian Hossa, RW, Chicago – 12 years, $62.8 million
Hossa’s was the blockbuster deal of the summer. The Blackhawks get a 30-year-old right winger with a penchant for 40-goal seasons, but the problem here is the cap implications such a deal has. The 12-year term means Hossa could count for $5.23 million towards Chicago’s cap until 2021, when he’s 42. The likelihood of Hossa hanging on that long is next to nil, but the Hawks now could be unable to afford the services of Jonathan Toews, Patrick Kane and Duncan Keith, all of whom must be re-upped next summer.

5. Mike Cammalleri, LW, Montreal – five years, $30 million
He’s versatile, but also small and has just two point-per-game seasons under his belt. Last season, his best as an NHLer, came alongside a superstar in Jarome Iginla. Asking Cammalleri, 27, to repeat such a performance in Montreal is too much. Here’s hoping he doesn’t just wilt under the pressure in the Canadiens fishbowl.

4. Nikolai Khabibulin, G, Edmonton – four years, $15 million
The cap hit - $3.75 million - isn’t a lot to pay for a starting netminder. But it is a lot to pay for one who is 36 and has had one decent season – during a contract year – since winning the Stanley Cup with Tampa Bay prior to the lockout. Khabibulin stole a few games last season and took his team to the conference final, albeit with a 2.93 goals-against average and .898 save percentage in the post-season. But what makes this deal a scary one is that, because Khabibulin is 36, his money cannot come off the Oilers’ books, retirement or not.

3. Martin Havlat, RW, Minnesota – six years, $30 million
The Wild divested itself of one oft-injured winger, only to sign another. Nobody will argue Havlat’s talent, but 2008-09 was the first season of his career he went the distance without missing an extended period due to injury. His past shoulder and head injuries are worrisome and there’s really no evidence to suggest one or both won’t pop up again and again, leaving the Wild wanting.

2. Brian Gionta, RW, Montreal – five years, $25 million
Sorry Habs fans, but are you really that surprised? Gionta, 30, is even smaller than Cammalleri and is on the downside, with his goals-scored total falling each season since he potted 48 coming out of the lockout. He’s speedy and feisty, but when he’s 34 and scoring 15 goals, will he be worth $5 million?

1. Marian Gaborik, LW, New York Rangers – five years, $37.5 million
After managing to move one onerous contract out of town (Scott Gomez), GM Glen Sather simply took on another. Gaborik will count for $7.5 million towards the cap (tied for seventh in the league), more than any other player signed this summer. Unfortunately for Rangers fans, you can expect him to not put up numbers worthy of such a cap hit. Gaborik will be a point-per-game player, but expect that to mean 60 points or so on average. He’s electric on the ice, but can’t stay healthy. Even more discouraging, Gaborik demonstrated a me-first attitude while working to get back to the battling-for-the-playoffs Wild when he admitted to not watching Minnesota games and worrying only about his return. A health risk and a seemingly selfish player; not a good mix.

Holland had been left in Toronto as the Maple Leafs opened a three-game western road trip in late November and has not suited up for the Leafs since Nov. 26. The 6-foot-2, 195-pound forward was a healthy scratch in 17 of the Leafs first 25 games this season.

In eight games, Holland has one assist and a minus-2 rating while averaging 10:43 in ice time a night. Holland is on a one-year, $1.3 million contract this season, and according to CapFriendly, is owed $881,111 for the remainder of the season.

"Peter is a big, solid centerman with good NHL experience," Coyotes general manager John Chayka said in a statement. "We look forward to having him join our team."

Acquired from the Anaheim Ducks in November 2013, the Caledon, Ontario native appeared in 174 games with the Leafs, over parts of four seasons, scoring 25 goals and 63 points.

The 25-year-old also played a role in the American Hockey League’s Toronto Marlies reaching a seventh game of the conference finals during the 2014 Calder Cup playoffs.

For the Leafs, the move gives general manager Lou Lamoriello another contract spot to work with. Prior to the deal, Toronto had 48 contracts – two shy of the maximum of 50.

Friday’s move gives the Leafs the flexibility to sign goaltender Karri Ramo to a contract for the remainder of the season. The 30-year-old signed a professional tryout with the Marlies on Tuesday and made 33 saves in 3-2 loss to the Utica Comets on Wednesday night.

Since waiving goaltender Jhonas Enroth on Tuesday, and assigning him to the Marlies, the Leafs are looking for a suitable veteran presence behind Frederik Andersen and Ramo could fill the void.

The trade with the Coyotes also gives Lamoriello roster flexibility to activate forward Josh Leivo off non-roster injury reserve. Leivo has yet to play this season due to a lower body injury. The 23-year-old played five games with the Marlies earlier in the season as part of a conditioning assignment, but was deemed not ready to return to NHL action with the Leafs.

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Coyotes’ Cunningham alert, awake and joking with teammates, but remains in hospital

There’s still no word as to what exactly caused Coyotes AHL captain Craig Cunningham to collapse on ice, but the 26-year-old was in contact with teammates and cracking jokes earlier this week.

More than two weeks after collapsing on the ice ahead of an AHL game between the Coyotes and Jets AHL affiliates, news has come that Craig Cunningham is starting to get back to his old self.

According to Tucson’s KVOA, Cunningham spoke with two teammates, Brandon Burlon and Christian Fisher, via FaceTime earlier this week, and both said that things are starting to look up for the 26-year-old Cunningham.

Fisher added that it was nice to see Cunningham, the captain of the Coyotes’ AHL affiliate Tucson Roadrunners, smiling again. But he wasn’t just smiling, he was also trying to have a good time with his teammates while hinting that he wants to get back on the ice.

“He was cracking jokes just as if he were here the next day," Fisher told KVOA. "It was pretty funny. He said he wanted us to come pick him up and take him to the rink. He was joking around. Stuff like that.”

The mystery still remains as to what caused Cunningham’s collapse, however. It came just moments before the game was set to start and resulted in medical staff in the building cutting away his equipment in order to attend to him. Cunningham ended up leaving the ice on a stretcher, was transported to hospital and he remained in critical but stable condition for much of the past two weeks.

Still, though, Burlon and Fisher said that there’s no “definitive answer” as to what caused Cunningham’s medical emergency. That’s more than all right with both players, too, so long as Cunningham’s health is starting to look up.

"What we do know is that he is doing well and we are moving forward here," Fisher told KVOA. "Hopefully, he will start the road to recovery now.”

Cunningham has suited up for 319 AHL games over the course of his career, netting 101 goals and 203 points, as well as scoring an additional three goals and eight points in 63 NHL games. He was drafted 97th overall by the Bruins in 2010, but was picked up by Arizona off waivers from Boston during the 2014-15 season.

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Passion drives Boston College coach Jerry York to go old school

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Passion drives Boston College coach Jerry York to go old school

Faced with the prospect of not being able to fly to a game this weekend, Jerry York wasn't about to let that stop him from coaching Boston College.

Back in the late 1970s, Jerry York was the youngest coach in the nation. Now he’s the second oldest, behind Red Berenson, who turned 77 yesterday. York is in his 45th season behind the bench of a Division I team and he’s coached a mind-boggling 1,740 games. He’s won 1,025 of them, which is exactly 100 ahead of Ron Mason, who’s No. 2 on the all-time wins list. He’s guided five national championship teams and put countless players in the NHL, from Hall of Famer Rob Blake to current NHLers such as Johnny Gaudreau, Cory Schneider, Brian Boyle and Patrick Eaves.

In other words, he had perhaps earned the right to sit this one out. The 71-year-old dean of Division I hockey could have told associate coach Greg Brown to take the bench for one night. But faced with the prospect of not being able to fly to South Bend, Ind., to coach his Boston College Eagles against Notre Dame Saturday night because he’s recovering from surgery to repair a detached retina, York instead went old school for the 900-mile, 18-hour journey.

While the rest of the team chartered out of Boston Friday afternoon for a 90-minute flight, York had his director of hockey operations, John Hegarty, drive him to Albany Thursday afternoon. From there, York hopped an Amtrak train bound for South Bend that got in at about 8:30 Friday morning. And the most stunning thing about all of this is that York did this coach one game, not a weekend series. In fact, he figures Saturday night’s game will go until about 10 p.m., which means he’ll be able to take an Uber from the Compton Family Ice Arena to catch the midnight train that will let him retrace his steps, meaning he should get back to Boston sometime Sunday evening.

York missed six games early in the season while he was recovering from the surgery, but wasn’t about to sit any more out. So there he’ll be Saturday night, behind the Eagles bench, sporting an eye-patch and trying to help his team improve on its 8-0-1 record in Hockey East. It’s already the best start of any team in league history, but that’s not what is motivating him. It’s the passion for coaching that still drives him.

“All I need is a parrot on my right shoulder and I’ll be a buccaneer,” York said. “I think for me, this was a telltale sign that I still want to do this, that I have the passion to do it. This was a key indicator, if I didn’t want to do it I think that would be telling me something. I see Red Berenson at coaching conferences and we both like golf and other things, but I’d still rather be coaching than doing anything else. I love being behind the bench and I love tying up my skates at 2:30 every day.”

And York has a lot to be excited about this season. Despite losing seven players to the NHL from last year’s team, the Eagles have been a Hockey East juggernaut this season. Despite losing seven underclassmen to the NHL, the Eagles are the top team in their league and with an overall record of 13-5-1 has them the No. 4-ranked team in the nation. They’re second in the NCAA in goals scored with 71 and their goal differential of plus-30 is No. 1 in the nation.

“We have 13 freshmen this year,” York said. “That’s a lot of new guys. We were prepared to lose maybe three guys (to the NHL), but we got surprised and we had to scramble. We had to almost rebuild the whole program.”

It has helped that freshman Joe Woll, a third-round pick of the Toronto Maple Leafs, has more than filled the void left by Demko. The 6-foot-4, 202-pound native of St. Louis has been the team’s backbone and a large reason why the Eagles have given up only nine first-period goals in 19 games this season. They’re also outscoring their opponents 28-12 in the second period. The Eagles are led offensively by a small, skilled kid by the name of Gaudreau from New Jersey, just as they were two years ago. Matthew Gaudreau, whose brother Johnny won the Hobey Baker Award with the Eagles three years ago and turned pro with the Calgary Flames, leads the team with 6-16-22 totals in 19 games.

“This isn’t the most talented team I’ve ever had,” York said, “but it’s the most enjoyable for me to coach in a long time.”

The game against Notre Dame will be the last before the holidays. That means York won’t have to get on a plane until a trip to Pittsburgh after Christmas. He sees his doctor Dec. 23 and hopes to be cleared to fly after that. If not, he’ll likely be on the train to Pittsburgh because he’s not about to let a long travel day keep him from behind the bench.

“It’s not in my fabric,” he said of the prospect of missing games. “I feel just like Punch Imlach.”

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Cal Clutterbuck’s five-year extension won’t bite the Islanders for a couple of seasons, but when it does, it could cost the Islanders more than just money and cap flexibility.

Cal Clutterbuck is on pace to have his highest scoring season as a New York Islander, he’s averaging more ice time than he has in any other year with the club and he was given an alternate captaincy ahead of the campaign.

And even with all that, it’s hard to understand how exactly the Islanders saw fit to have the 29-year-old winger a five-year, $17.5-million extension.

Clutterbuck is undoubtedly one of the best at playing the specific role he plays, which is to say that if you’re looking for a hard-nosed player who’s going to put his body on the line, he’s your guy. Fans love him, teammates assuredly do, too, and he’s exactly the kind of bottom-six player that most GMs around the league would love to have on their team at the right price.

Problem is that it’s really tough to call $3.5 million per season the right price, and that’s exactly what Clutterbuck will be earning come the start of the 2017-18 campaign. That’s roughly the same cap hit as others such as Kyle Turris, Cam Atkinson, Joel Ward and Matt Read will be carrying next season, and that’s only to name a few.

Another worrisome part about the deal is that it’s hard to see how even the biggest fitness freak could maintain their ability to play Clutterbuck’s style into their mid-30s. The wear and tear on Clutterbuck’s body by the time he reaches the back-end of the contract could be substantial. Despite him playing up the lineup right now, he’s better suited to a bottom-six role and definitely will be later in his career. If he loses a step, $3.5 million will be a lot to fork over for a fourth-line winger and it’ll be a deal that’s near impossible to move.

But it goes beyond simply the signing of Clutterbuck, because there has now been a trio of deals handed out by Islanders GM Garth Snow that have been puzzling — and, truthfully, concerning — when it comes to the future of the team.

Ahead of free agency, there was the signing of Casey Cizikas to a five-year, $16.75-million deal. Then came the monster seven-year, $38.5-million contract inked by free agent Andrew Ladd. The Clutterbuck signing is No. 3.

It should be noted that the deals for Clutterbuck, Cizikas and Ladd don’t actually prevent the Islanders from doing all that much in the next two seasons. In fact, as of next season, every single current Islander forward will be locked up to a contract. Come 2018-19, when John Tavares becomes a free agent, the slate is wiped rather clean with the team able to operate with more than $40 million in cap space. Beyond Tavares, the Islanders’ UFAs come 2018-19 will include Josh Bailey, Nikolai Kulemin, Jason Chimera, Mikhail Grabovski and Thomas Hickey.

And $40-plus million can buy you a lot, and certainly it will allow the Islanders to hang on to Tavares, if he chooses to remain with the team. (Not to say he won’t, but a lot can happen between now and July 2018.) All the UFAs, save maybe Bailey and Hickey, will be allowed to head elsewhere, as well. A restricted free agent deal for Brock Nelson could be pricey, but the Islanders should realistically be able to lock him up. As of right now, the Islanders will also be without an NHL goaltender under contract, but there will be stop-gap options available. So, yes, the Islanders should be fine in 2017-18 and 2018-19.

However, things could get dicey after that.

Come 2019-20, the Islanders will watch Travis Hamonic become a UFA, see the end of entry-level deals for Mathew Barzal, Anthony Beauvillier, Joshua Ho-Sang and Michael Dal Colle and still have more than $12.3 million locked up in Ladd, Cizikas and Clutterbuck. Finding the money to lock up those five players, as well as any others who could be seeking new contracts around that time, will be incredibly difficult.

The cost of those trio of deals goes beyond money and cap space, though, because there’s a serious possibility the Islanders could waste some of the best years of Tavares’ career. If the Islanders can only afford to hang on to the pieces they have without being able to add any veteran or prime-aged players, it gets hard to see how this franchise takes the next step forward, even with Tavares in his prime.

They’ll need a few adds on defense, a few forwards who can contribute and the goaltending situation will need to be figured out. Ilya Sorokin should give Islanders fans hope, but even the best goaltending prospects sometimes don’t pan out in the big league. If the Islanders need to improve in goal when their prospects are hitting their stride, the money spent in the past seven months could very well prevent that from becoming a reality.

It’s big-money, head-scratcher deals like Clutterbuck’s that teams have had to buy their way out of in the past, and it’s scary to think the Islanders could have set themselves up for the same fate three times over. The Islanders' post-season performance was reason for excitement, but now it seems, more than anything, there's cause for concern about what the future could hold.